Reaction #1483030

Reaction equation

4-(tert-butyidiphenylsilyloxy)butan-1-ol

Dess-Martin periodinane

→

4-(tert-butyidiphenylsilyloxy)butanal

Solvents

—

hexanes

—

hexanes

dichloromethane

dichloromethane

Conditions

Workup

1. 1
   Otherthe resulting white precipitant was removed via filtration
2. 2
   ConcentrationThe solution was concentrated
3. 3
   Otherto give
4. 4
   Otherform a slurry, which
5. 5
   OtherThe solids were removed via filtration
6. 6
   Concentrationthe resulting solution was concentrated

Procedure

To a solution of the 4-(tert-butyidiphenylsilyloxy)butan-1-ol (0.5 g, 1.5 mmol) in dichloromethane (20 mL) was added Dess-Martin periodinane (775 mg, 1.83 mmol). The mixture was stirred for 1 h. The reaction mixture was poured into hexanes and the resulting white precipitant was removed via filtration. The solution was concentrated to give form a slurry, which was dissolved in dichloromethane (5 mL) and again poured into hexanes resulting in the precipitation of white solid. The solids were removed via filtration and the resulting solution was concentrated. This gave 475 mg (97%) of a clear oil: 1H NMR (CDCl3); δ1.04 (s, 9H), 1.89 (m, 2H), 2.55 (m, 2H), 3.69 (t, 2H, J=6.1 Hz)), 7.38 (m, 6H), 7.63 (d, 4H, J=1.7 Hz), 9.79 (t, 1H, J=1.8 Hz).

Source